Diacrylate oligomers were synthesized via a base-catalyzed thiol-Michael addition in a manner similar to those previously reported (34). In an open 100-ml round bottom flask with a mechanical stir bar, butylated hydroxytoluene (9 mg, 1000 ppm), RM82 (6625 mg, 9.858 mmol), and NPGDA (1046 mg, 4.929 mmol) were dissolved into DCM (30 ml, 0.5 M), followed by the addition of allyl dithiol (1600 mg, 13.308 mmol). TEA (8.24 ml, 59.14 mmol) was added, and the reaction mixture was allowed to stir for 16 hours, followed by the removal of DCM and TEA in vacuo. The resulting viscous liquid was dissolved in DCM (200 ml) and washed with 1 M HCl (2×, 100 ml) and brine (1×, 100 ml), followed by drying with sodium sulfate and removal of DCM in vacuo, which produced a white semisolid resin. NMR was used to confirme the consumption of thiols and determine the average number of repeat units through end group analysis of acrylic protons compared to allylic allyl sulfide protons. A molar ratio of 1:0.5:1.35 (RM82/NPGDA/allyl dithiol) was used for all results shown unless explicitly stated.

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